Live, Love, & Play in Blythewood Estates a private enclave near premier Lake Onota to experience idyllic living in the Berkshire hills. This stunning modern 6000+ sf, 5 Bedroom, 5.5 bath colonial is thoughtfully designed and beautifully set on 3.42 manageable acres with sweeping meadow views nestled perfectly to create peace in nature while centrally located minutes to the culture, arts, museums, fine and eclectic dining and central to Tanglewood and The Clark Art. Three levels of living create a blend of fun and entertainment with a degree of separation on levels. First floor offers one level easy living with a dramatic two story primary bedroom suite. Second floor boasts heightened enjoyment with four spacious bedrooms spanning a second story balcony. Lower level offers a theatre, gym

Designed in 1929 by noted architect Henry Seaver (Berkshire Museum, Lenox Town Hall), this distinguished Georgian Colonial was once the centerpiece of Pittsfield's social scene. The home preserves exquisite 18th-century details - mantels, wainscoting, and finely crafted woodwork salvaged from two of the city's earliest residences, making it a living piece of Berkshire history. Set back on 2.5 private acres along prestigious Crofut Street, the estate offers 5 bedrooms and 5 baths, including twin primary suites ideal for hosting friends and family year-round. Gracious living and dining rooms, a peaceful sunroom, a cozy study, and a large eat-in kitchen with Viking range and butler's pantry combine period elegance with modern comfort. This turn-key estate is offered fully furnished and

Properties of this magnitude and character are becoming a true rarity in today's market. Brookmede Farm, isn't just a listing; it is a magnificent blank canvas of 22 beautiful scenic acres, defined by sweeping mountain views and a profound sense of quiet serenity. From the moment you arrive, the silence and the scale of the landscape invite you to imagine the unlimited possibilities. Whether you envision a world-class equestrian estate, a sustainable organic farm with cows and chickens, or a sophisticated multi-structure family compound, this land provides the space and the soul to make it a reality. Standing as a centerpiece to this vision is a towering, three-story Timber Frame barn. With its incredible volume and structural presence, it offers a

Professionally redesigned, this contemporary residence w/ deeded water access, blends luxury Lake Garfield summer living and a modern ski chalet winter experience. The unique architecture captures lake views from expansive decks and oversized windows. The move-in-ready home is filled with natural light and features wood floors, a designer kitchen, a sauna, 4 full baths, 4 beds plus office/den, and 2 living rooms, each with a wood-burning fireplace. Mini-splits throughout provide cooling. Outside, enjoy a fully fenced, private yard w/ a hot tub and fire pit seating area. The lake access is ideal for kayaks and paddleboards, swimming or mooring your boat. The property is by Butternut ski mountain, hiking and only 15 min from bustling Great Barrington. Turnkey, sophisticated & ready to enjoy.

Beautifully renovated inside-out from 2018-2021, this elegant Victorian on Great Barrington's coveted ''Hill'' retains period charm with every modern comfort. The sun-filled layout features a generous eat-in kitchen with custom cabinetry, three-plus bedrooms, 31/2 baths with heated floors, gorgeous wood flooring throughout, and a high-efficiency wood-burning fireplace anchoring the main living room. A Vits-designed office and mini-splits on every floor complete the picture. The charming garage studio -- with its own full bath, kitchen, and Stuv wood stove -- offers endless possibilities as a guest/entertainment retreat, creative workspace, or home office. All on a rare corner lot of .37 acres, the property is fenced and framed by mature landscaping that provides privacy & shade. More...

Located in Stockbridge, this historic General Williams House (circa 1795) has been restored and updated. Featuring 6 bedrooms, 5.5 bathrooms, 6 beautiful wood burning fireplaces, large dining and living spaces and 2 kitchens. THIS PROPERTY HAS AN EXCELLENT HISTORY OF RENTAL INCOME. The ''Ice House'' features its own kitchen and bath, for family gatherings or as Artist Studio. A sparkling in-ground pool for your summer pleasure. All this and more exists close to Main Street Stockbridge, Norman Rockwell Museum, Tanglewood, and all the most important cultural amenities. Rental income? This property has a very nice history of rental income! Who could ask for anything more? Call for a showing today.

WHISPERING PINES. This tranquil property will call to you as you wind your way through the tall pine-lined driveway. It is a very private setting and just minutes to Butternut, town, and everything else the Berkshires have to offer. Beautiful mature gardens, Gunite Pool, screen porch, and 3600 sq ft of living space to dwell. This 4 bedroom home has 2-Primary en-suite, a large den over the 2-car attached garage. First floor office space or overflow room for guests. A newer first floor Primary Suite wing added in 2017 boasts a very large walk-in closet, steam shower and an ample-sized bedroom. The expansive screen porch looks out on the yard, pool, yard and gardens. Partially finished will easily help you expand upon this magnificent home. A second 2-car garage for enhanced storage space.

This impressive Italianate residence, dating back to 1880, has been meticulously restored for modern, turn-key living. This coveted location with a private backyard and off-street parking neighboring Talbot & Arding - offers a rare sense of quiet just a few blocks from the restaurants, galleries, and shops of the exciting city. Spanning three thoughtfully renovated stories, the turn-key property includes a large eat-in kitchen, sunny, and bright living and dining room, and a large mudroom. The top two floors contain bedrooms and bonus spaces ideally suited for year-round living and guest suites. The showcase of the home is the gorgeous staircase with a curved banister that enhances all three floors. Outside, there is a private backyard and side patio and a staircase to lower Hudson.

A rare opportunity awaits! Own a developable mountain top in the Berkshires! Your 4B/2.5Bath home is 10 years young with custom kitchen and baths. An unobstructed view of Goose Pond and beyond, it's a 56 acre sanctuary mostly comprised of Oak and Mountain Laurel forest with trails. Enjoy a 40 mile view to Mt. Greylock and views of October Mt. State Park, and boating on Goose Pond (@1/2 mile to the the boat launch). Also viewable is Tyringham Valley, South Lee and Bear Town State Forest. Build another home on the property (ADU or a larger home and keep this as your guest house). Possibilities are endless here! Already in place is a 28'X48' building with 14' ceilings with it's own electric service, (could also be used for horses) and a small barn near the house. A one of a kind offering.

Sited at the highest point in Hillsdale this modern home captures the world around while being incredibly private. Main house has tall ceilings tremendous natural light and doors bringing you outside from every space. Music room on the east side captures the Berkshire hills with doors out to the breakfast patio. Office with en suite is off the entry. Second floor is the primary suite; everywhere you look you stop to take in the view, large bath with walk-in closet and laundry. The inner courtyard has a heated pool, sunken jacuzzi, outdoor shower, screen porch with fireplace and beautiful perennial gardens. Hidden off the drive is a guest cottage with open living area, bedroom and full bath.

Beautifully restored historic Colonial on a lightly traveled, town maintained road with stone walls, fruit trees, open meadow, wooded acreage, and a barn or garage. Bordering protected land and offering about a mile of road frontage, the setting feels private, quiet, and deeply rooted. Long associated with author Simon Winchester, this is a rare Berkshire antique with depth, authenticity, and lasting appeal. c.1760 and 1840. 4 bedrooms, 3 baths. Library, keeping room with original crane fireplace, Aga kitchen, vaulted living room, screened-in porch. A c.1812 granary rebuilt as a writing studio with loft and full bath. Stone walls, orchard, meadow, vernal stream. 50 acres. 3/4 mile road frontage. Borders protected land. A setting that feels sheltered, rooted, and quietly beautiful. CLICK

A completely transformed barn renovated into a chic home with every modern convenience. Located in the desirable town of Egremont and just minutes from Great Barrington, this delightful property offers long-range pasture views with direct Green River waterfront.Thoughtful living spaces for every walk of life featuring a roomy primary suite on the first floor, an additional primary suite that occupies the entire third floor, and inviting spaces for guests and gatherings. Key features include top brands like Waterworks, Wolf, Schluter, Graff, Bertazzoni, and Kohler, along with Danby marble, Italian tile, and oak floors. Every window offers views of the expansive 13.5 acres, fully fenced and lush, with endless possibilities for nature lovers, hobby farmers, or equestrians. Super low taxes.

Nestled on the top of a hill overlooking rolling meadows, this exceptional property boasts over 30 acres of stunning natural beauty, with panoramic 360-degree views that will take your breath away. A true oasis of tranquility, this estate offers the ultimate in luxurious country living. The grand foyer invites you into this warm, inviting home. With over 6,000 square feet of living space, it offers plenty of room to entertain and relax. The large cook's kitchen is perfect for preparing meals for large gatherings, while the heated sun room provides a cozy spot to enjoy your morning coffee and take in the stunning views of the surrounding fields. This home also features 5 spacious bedrooms (primary with en-suite, four jack-and-jill), each with their own unique charm and character.

Hawks Nest Ridge. Quiet privacy on 8.6 acres. Decks, patio, screened porch and pool all enjoy the view and the natural setting. Dramatic open floor plan with walls of windows to the views, soaring stone wood burning fireplace spanning three stories. Cook's kitchen with walk-in pantry. First floor primary suite with gas fireplace and dressing room all abutting library and office. 4 private bedroom suites in total each with their own sitting areas (additional sleeping options possible). Family room with wet bar and gas fireplace. Exercise room with steam shower. 3-bay garage. A very special retreat with plenty of room for guests and entertaining. Just a short jaunt to dining, shopping, recreational and cultural venues in West Stockbridge, Lenox, Stockbridge and Great Barrington.

Set on over 12 private acres just minutes from the center of Great Barrington, this impeccably designed estate offers an extraordinary combination of luxury, privacy, and panoramic southern views of the Taconic Range, including the iconic silhouette of Mount Everett. Blending effortless indoor elegance with immersive outdoor living, this property captures the essence of Berkshire leisure. Inside, the home is thoughtfully designed to host both family and guests in complete comfort, offering five well-appointed bedrooms, six full bathrooms, and a half bath, providing privacy and ease for all. The first-floor primary suite serves as a true sanctuary, complete with two separate full bathrooms for an elevated sense of luxury.

Stunning Views! Exquisite Tudor-style stucco estate set on more than 18 breathtaking acres with panoramic views and a winding approach that creates an extraordinary sense of arrival. Bright, airy, and thoughtfully designed, this 5-bedroom, 5-bath residence blends timeless architecture with modern comfort and exceptional indoor-outdoor living. The heart of the home is a stunning great room featuring soaring ceilings, abundant natural light, and hardwood floors throughout. An open-concept layout flows seamlessly into the generous chef's kitchen, complete with a professional-grade gas range, spacious dining area, and direct access to the expansive deck overlooking the rolling landscape. The main-level primary suite offers privacy and convenience with a spacious bath and ....

Welcome to an extraordinary lakefront estate on the shores of Pontoosuc Lake, an offering that sets a new benchmark for luxury living in the Berkshires. With over 7,494 square feet of total space, including exceptional garage capacity ideal for car collectors or hobbyists, this remarkable property offers unparalleled scale, versatility, and setting.The main living area showcases a thoughtfully designed open floor plan that flows seamlessly toward the water, ensuring the views are always front and center. Enjoy sweeping northern-facing vistas of Pontoosuc Lake, Mount Greylock, and the surrounding Berkshire hills. Whether relaxing on the expansive deck, swimming in the in-ground pool, or departing from your private dock, the connection to nature and water is ever-present.

Beautifully sited to capture light and long-range views, this architect-designed residence offers timeless elegance within a serene natural setting. Bright, sophisticated interiors open seamlessly to a screened porch and stone terraces overlooking the pool and manicured grounds. Generous proportions and refined architectural details define the living spaces, complemented by a beautifully reimagined library/office, dining, living media/den and kitchen. First-floor primary suite serves as a private retreat, while additional en-suite bedrooms provide comfort and discretion for guests. An upper-level loft (w/ elevator)offers space for gym, studio, or media. A rare offering of privacy, design, and distinction in the Berkshires.

East Hill Farm offers 227 acres of protected quiet, anchored by the elegant 1798 Thomas Shepard House. A private hilltop world. Main house: Georgian-Federal; 5 BR, 5.5 BA, ~5,000 SF; 5 fireplaces; unusually high ceilings, wide-board floors, antique glass, rooms that hold the light, views that connect. Graceful, welcoming. A complete estate that also can be a working-farm or equine property: barns + outbuildings, pastures, private trails + roads, 4+ acre pond, gardens + orchard, pool, pool house, greenhouse, tennis. A vast former Arabian horse barn, now guest compound, or for you to reimagine. Preserved with rigor, lived in with joy, and rooted in the land and history that defines the Berkshires. Read the whole story. Read the whole story - Click!